3-((2S,3S,4S,5S)-3-((1S,2S)-1-(benzyloxy)-2-methylbutyl)-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxamido)propanoic acid

ID: ALA2315999

Chembl Id: CHEMBL2315999

PubChem CID: 71496730

Max Phase: Preclinical

Molecular Formula: C27H35N3O6

Molecular Weight: 497.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](OCc1ccccc1)[C@H]1[C@H]([N+](=O)[O-])[C@H](c2ccccc2)N[C@]1(C)C(=O)NCCC(=O)O

Standard InChI:  InChI=1S/C27H35N3O6/c1-4-18(2)25(36-17-19-11-7-5-8-12-19)22-24(30(34)35)23(20-13-9-6-10-14-20)29-27(22,3)26(33)28-16-15-21(31)32/h5-14,18,22-25,29H,4,15-17H2,1-3H3,(H,28,33)(H,31,32)/t18-,22+,23-,24-,25-,27-/m0/s1

Standard InChI Key:  WSUFYWDDGAKRPT-NVQOMKKLSA-N

Alternative Forms

1. Parent:

   

   ALA2315999

   3-[[(2S,3S,4S,5S)-2-methyl-3-[(1S,2S)-2-methyl-1-phenylmethoxybutyl]-4-nitro-5-phenylpyrrolidine-2-carbonyl]amino]propanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 497.59

Molecular Weight (Monoisotopic): 497.2526

AlogP: 3.57

#Rotatable Bonds: 12

Polar Surface Area: 130.80

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.53

CX Basic pKa: 7.06

CX LogP: 1.61

CX LogD: 1.13

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: -0.11

References

1. San Sebastián E, Zimmerman T, Zubia A, Vara Y, Martin E, Sirockin F, Dejaegere A, Stote RH, Lopez X, Pantoja-Uceda D, Valcárcel M, Mendoza L, Vidal-Vanaclocha F, Cossío FP, Blanco FJ..  (2013)  Design, synthesis, and functional evaluation of leukocyte function associated antigen-1 antagonists in early and late stages of cancer development.,  56  (3): [PMID:23339734] [10.1021/jm3016848]

Source

Source(1):

• Scientific Literature